


When being bad is so good it loops all the way back around to being bad again

by SassMaster99



Series: Teen Wolf Sterek [1]
Category: Dom Derek - Fandom, Sterek - Fandom, Sub Stiles - Fandom
Genre: M/M
Language: English
Status: Completed
Published: 2020-03-23
Updated: 2020-03-25
Packaged: 2021-02-28 23:21:58
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 2,069
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23285449
Author URL: https://archiveofourown.org/users/SassMaster99/pseuds/SassMaster99
Summary: Stiles was only quiet for him. Until he can’t control himself anymore. Derek may have to prove to Stiles that Derek is the main person he should hold his tongue around. Unless, of corse, he likes choking on his own spit in his mouth.
Relationships: Derek Hale/Stiles Stilinski
Series: Teen Wolf Sterek [1]
Series URL: https://archiveofourown.org/series/1674709
Comments: 1
Kudos: 15





	1. Chapter 1

Derek likes it best when his boy takes his punishment like the good boy he is. Stiles would do or give anything to make Sir happy. Even if that involves wearing a cock ring while Derek teases him until he is about ready to pass out. But like always he is nice before he is mean. So at this moment Stiles has his hands and arms tied behind his head at an angle that is torture within itself. Derek of corse knows this which is why he takes so much pleasure in punishing and torturing Stiles simultaneously with the pleasure he is not allowed to experience. This whole thing is not really fair considering the fact Stiles is tied up while Derek just has his way with him. He can cum and cum though while Stiles is left without the sweet relief. Derek normally makes it worth his while but as Derek is spanking Stiles, he is not really sure how it would or could ever be worth this. Stiles is fighting the tears in his eyes from the overstimulation from the vibrator inside him and the raw feeling coming from his ass. Werewolf strength is not something to be messed with. Derek of corse gagged him with this thing that forces his mouth into an O that is barely big enough for Dereks dick. Stiles knows this ring couldn’t handle Derek's cock when his mate is in heat. But then again Derek wouldn’t tie him up like this if Stiles or Derek were in heat. Since Derek likes to walk the line between to much and not enough. He could either be all over you or tie people up getting off on watching them struggle. Stiles never thought he would wish for all the sensations to stop this much. Or maybe he just wants this damn cock ring to be off. Like Derek knows what he’s thinking Derek licks his mouth around both the cock ring and the rest of Stile’s dick. Making Stiles break composure and start whining. Derek sucks on his dick and takes the ring off. Stiles lets out a breath he didn’t know he was holding. Derek gets very close to his face. He nips at stiles nose and whispers in his ear if he would like to get fucked with Derek's monster cock. Stiles eyes roll up into his head as he says, “Please yes, Sir” Derek smiles because he would do anything for his boy. Stiles finds himself face down ass up as Derek makes sure he can handle Derek’s dick. Stiles breaks again making begging noises to which Derek Slams himself into Stiles greedy ass. Stiles almost loses it and comes apart right there. He holds it together losing it on the next few thrusts though. He falls apart, falling into Derek’s chest. Derek holds him. Derek whispers in his ear that he is such a good boy and this is just the beginning of what he’ll do to Stiles in the weeks to come.


	2. Pain Leads to Pleasure

**Summary for the Chapter:**

> Naughtiness leads to pain which leads to pleasure again as long as some people just remember they have werewolf strength. Stiles just wonders if he will make it through this.

(A few days later) Stiles can't stop. He wishes he could but he can't and really he blames Derek. That stupid, hot idiot has done this to him. In no way could you ever say this was for him. For Derek it was a good time but then he leaves. Stiles is alone and maybe his heat is approaching because he needs it. So if Derek were to walk in on him right now Stiles wouldn't even be flustered at this point. He NEEDS it which is really sad but he can't seem to control himself. He doesn't know how Derek went to work leaving Stiles here. He looks around for his phone, finds it, and proceeds to send the dirtiest pictures to Derek asking to be punished almost. Stiles can just picture Derek at work expecting the text from stiles to be something sweet or one of his jokes. Not what is contained in the message. In the picture Stiles is on his knees showing how bendy he is because the picture shows him contorted to see his flushed cock and his gaping hole with nothing filling it.  
Derek looks at this text, can't breathe for a few minutes and texts back where the toys are located in their house. He receives another text from Stiles that is another picture of Stiles with a huge Derek size dildo shoved to the hilt in his ass. Derek leaves work as quick as possible. He headed straight home and finds Stiles a mess in their room. Derek tells him he will be right back and runs to retrieve the present he just got for Stiles. Derek walks back into the bedroom with a wrapped couple of boxes he sets by Stiles to open. Stiles can't breathe and is on the verge of tears as he picks one up and starts opening it. He slides out a huge dildo that looks odd. Derek explains that it can be frozen and has a vibrator in it and sees the glee light up on Stiles face and in his eyes. He opens the next packager and finds a whip and a flogger that he is not to sure about but he decides anything for his dom.  
In the last box, which Stiles timidly open after he didn't really love the last one, he finds cream and lotion. He looks at Derek to which the Alpha just mumbles something about after care and not wanting to hurt him. This of course makes Stiles blush and want to hide. Derek doesn't give him a chance by grabbing him and tying him down spread eagle on a table where he's at Dereks mercy. Stiles is blind folded to his horror as Derek drags the ends of the flogger over his skin. Stiles tries to say something that will snap Derek out of it.  
But all this effort gets him is a ball gag shoved into his mouth. Derek drags the flogger on him one more time before the swats start coming. The first one stings so bad tears come to Stiles eyes but he endures. The second hit makes him gasp around the gag. By the third and fourth he doesn't even react until the sixth mostly hits his balls and cock. Derek sees this and hits him there again. "You CAN NOT send those kind of pictures to me" he says sternly. Stiles makes a noise to which Derek hits him again and says," Maybe this will teach you to be silent when we play. Stiles gets hit about ten more times after Derek says this and just can't until Derek unties him and starts rubbing lotion into his skin. Derek tries to soothe him and it works along with him sinking to his knees and giving Stiles a blow job that he swallows all down.  
He pops off and runs over to the freezer where he grabs the freezing dildo and saunters back to Stiles where he licks him out and stretches him till he slides the toy inside. Stiles can't breathe because as bad as the punishment was this might be worse. That is until Derek turns it on and then its like the dumb thing know exactly where he is weakest. He orgasms from it once building to a second one When Derek shuts it off and removes it replacing it with his warm cock that reaches spots that dildo cold only hope to reach. Derek laughs and slams his whole length back into Stiles after fully removing it. He does this until Stiles is coming apart again around his length. Derek won't stop now though as he gets at least three more orgasms out of him until he literally can't anymore. He is a babbling mess that Derek just picks up and takes to the bedroom with him again. Derek tucks Stiles limp form into bed with him and drapes him over his broad chest.


	3. Switching Backfires

**Summary for the Chapter:**

> When they think that they can switch but once a sub always a sub.

Derek walks in the room only to see Stiles still passed out on the bed. He sighs and figures that this much kinky sex must have exhausted the younger boy. He has another idea but knows it is another level of crazy. He would probably not want to anyway considering how vulnerable he is when he can barley speak from all the pleasure he feels. But there is only one way to know for sure and that would include having Derek say words he would have thought he never would have to or want to utter. This would include Stiles waking up which Derek may help along just a little. In Dereks defense it wasn't him with the morning wood first. Stiles is just making little moaning noises in his sleep and the blankets begin tenting. How could Derek resist? He pulls the blanket aside to reveal Stiles dick throbbing and just begging for Derek to lick the pre-cum off the top and swallow him down whole. This of course makes him even harder if that is possible until his hands are fisted in Dereks hair until he is finished and is greedily kissing Derek tasting his cum on his lips.  
"That was a nice way to wake up", he says.  
Derek chuckles wondering if he is going to like this idea or not. Stiles just looks at him and peppers his skin with little kisses that start out sweet and then start verging on vulgar. Derek takes a deep breathe and mumbles something into Stiles chest. Stiles eases him away making him repeat it.  
Derek sighs saying," That he was wondering if Stiles would like to have a three or four way." To which Stiles just sits there dumbfounded.  
"Who?", he asks figuring already he won't like the answer considering Dereks dating history.  
"Well, you and me obviously and maybe Peter or Scott or something." He mumbles hoping Stiles says no. Stiles just get this sick look on his face. Mumbling something about liking it just being them and some rope.  
Stiles says," If you are getting that bored we could try tying you up." Derek looks at him with his amazing eyes and Stiles tacks on a "Sir" very quickly to the end.  
Derek surprises them all by nodding his head. Stiles just looks at him not sure what to do first. He passes his hand over the whips heading straight for a gag and a vibrator swearing to himself never to use the whips and settling on a gag that Stiles can thrust into knowing he had this O gag in his very mouth just days ago. But Stiles starts slowly not wanting to over do it at first but Dereks tongue and mouth know exactly what they are doing as they milk him again and again until Stiles can't even take the weight from the air touching him. He refuses to give up or let this backfire and ties Dereks hands over his head puts a vibrator against Derek's prostate and starts trying to suck him dry but he seems to never tire much to Stiles disappointment. That fact doesn't get Stiles to stop trying until Derek feigns that it hurts just to get Stiles to stop. He hopes Stiles feels victorious now though as he gets done Derek shoves a vibrator against Stiles prostate taking the remote with him. Derek buts it on the first setting smiling at the thought of Stiles not being able to get off and wondering how much he can torture his silly sub.  
Derek turns the controller up a few times throughout the day finding it hilarious when Stiles is dancing while he is making dinner and Derek puts the controller on eight. Stiles is practically begging Derek to fuck him but he just puts the controller on four and smirks to himself seeing the flush high on Stiles cheeks. Derek motions for stiles to strip until all he has on is the panties holding the vibrator in place. Stiles has to ask for permission to orgasm this time and he swears Dereks favorite word is no. While they eat Derek turns it up to setting nine and makes sure that when he finally lets Stiles cum he will sleep for a week. He takes Stile breath away with setting 10 and tells him he can cum and Stiles doesn't hold back. He has to be seeing stars as he collapsed into sleep.


End file.
